Tuberculatin analogs as antiviral agents

Abstract

Provided herein are tuberculatin analogs that are useful as antivirals, such as anti-HIV, anti-coronaviral, anti-Ebola viral, and anti-influenza viral agents and methods of use thereof.

What is claimed is: 
     
         1 . A compound of Formula I: 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt thereof, wherein: 
         X is oxygen or sulfur; 
         R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9  are each independently hydrogen, alkyl, akenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, aralkyl, heteroaryl, haloalkyl, halogen, cyano, NO 2 , —OR 26 , —C(═O)R 27 , —C(═O)N(R 26 )R 27 , —C(═O)OR 26 , —OC(═O)R 26 , —OSi(R 25 )(R 26 )R 27 , —S(═O) 2 R 26 , —S(═O) 2 N(R 26 )R 27 , —N(R 26 )R 27 , —N(R 26 )N(R 26 )R 27 , —N(R 26 )C(═O)R 27 , —N(R 26 )S(═O) 2 R 27  or a moiety comprising 1 to 30 plural valence atoms selected from the group consisting of carbon, nitrogen, oxygen and sulfur; or R 1  and R 2 , R 2  and R 3 , R 3  and R 4 , R 5  and R 6 , R 6  and R 7 , R 7  and R 8 , or R 8  and R 9  taken together with the carbon atoms to which they are attached to form a cyclic group which is optionally substituted with halogen or a moiety comprising 1 to 30 plural valence atoms selected from the group consisting of carbon, nitrogen, oxygen and sulfur; 
         R 10  and R 11  taken together form oxo; or while one of R 10  and R 11  is hydrogen or halogen, the other one of R 10  and R 11  is selected from the group consisting of R 25 , —OR 25 , —C(═O)R 25 , and —C(═O)OR 25 ; 
         R 12  and R 13  taken together form oxo; or while one of R 12  and R 13  is hydrogen or halogen, the other one of R 12  and R 13  is selected from the group consisting of R 25 , —OR 25 , —C(═O)R 25 , and —C(═O)OR 25 ; 
         R 19  and R 20  taken together form oxo; or while one of R 19  and R 20  is hydrogen or halogen, the other one of R 19  and R 20  is selected from the group consisting of R 25 , —OR 25 , —C(═O)R 25 , —C(═O)OR 25 , —OC(═O)R 25 , —OC(═O)N(R 25 )R 25 , optionally substituted monosaccharide, optionally substituted disaccharide, optionally substituted trisaccharide, and optionally substituted tetrasaccharide; 
         R 21  and R 22  taken together form oxo; or while one of R 21  and R 22  is hydrogen, halogen, R 25  or —OR 25 , the other one of R 21  and R 22  is selected from the group consisting of R 25 , —OR 25 , —OC(═O)R 25 , —OC(═O)N(R 25 )R 25 , —C(═O)OR 25 , —CH 2 R 29 , —CH 2 OR 29 , —C(═O)R 29 ; or R 19  and R 21  taken together with the carbon atoms to which they are attached to form a 5-6 membered heterocyclyl optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from R 25 ; 
         R 23  and R 24  taken together form oxo; or while one of R 23  and R 24  is hydrogen or halogen, the other one of R 23  and R 24  is selected from the group consisting of R 25 , —OR 25 , —C(═O)R 25 , —C(═O)OR 25 , optionally substituted monosaccharide, optionally substituted disaccharide, optionally substituted trisaccharide, and optionally substituted tetrasaccharide; 
         R 25  for each occurrence is independently selected from hydrogen, halogen, trichloromethyl, trifluoromethyl, cyano, nitro, —OR 26 , —C(═O)R 27 , —C(═O)N(R 26 )R 27 , —C(═O)OR 26 , —OC(═O)R 26 , —OSi(R 25 )(R 26 )R 27 , —S(═O) 2 R 26 , —S(═O) 2 N(R 26 )R 27 , —N(R 26 )R 27 , —N(R 26 )N(R 26 )R 27 , —N(R 26 )C(═O)R 27 , —N(R 26 )S(═O) 2 R 27 , —N 3 , —OS(═O) 2 CF 3 , hydrocarbyl optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from the group consisting of R 28 , heterocyclcyl optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from the group consisting of R 28 , and —(CH 2 ) k -heterocyclyl optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from the group consisting of R 28 , wherein k is an integer between 1 and 6; 
         R 26  and R 27  for each occurrence are each independently hydrogen or selected from hydrocarbyl and heterocyclyl, either of which is optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from halogen, cyano, amino, hydroxy, C 1-6  alkyl and C 1-6  alkoxy; 
         R 28  for each occurrence is independently selected from halogen, trichloromethyl, trifluoromethyl, cyano, nitro, oxo, ═NR 26 , —OR 26 , —C(═O)R 27 , —C(═O)N(R 26 )R 27 , —C(═O)OR 26 , —OC(═O)R 26 , —OSi(R 25 )(R 26 )R 27 , —S(═O) 2 R 26 , —S(═O) 2 N(R 26 )R 27 , —N(R 26 )R 27 , —N(R 26 )N(R 26 )R 27 , —N(R 26 )C(═O)R 27  and —N(R 26 )S(═O) 2 R 27 ; and 
         R 29  for each occurrence is independently selected from hydrogen, halogen, trichloromethyl, trifluoromethyl, cyano, nitro, —OR 26 , —C(═O)R 27 , —C(═O)N(R 26 )R 27 , —C(═O)OR 26 , —OC(═O)R 26 , —OSi(R 25 )(R 26 )R 27 , —S(═O) 2 R 26 , —S(═O) 2 N(R 26 )R 27 , —N(R 26 )R 27 , —N(R 26 )N(R 26 )R 27 , —N(R 26 )C(═O)R 27 , —N(R 26 )S(═O) 2 R 27 , —N 3 , —OS(═O) 2 CF 3 , optionally substituted monosaccharide, optionally substituted disaccharide, optionally substituted trisaccharide, optionally substituted tetrasaccharide, hydrocarbyl optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from the group consisting of R 28 , and heterocyclyl optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from the group consisting of R 28 , with the proviso that the compound of Formula I does not include a compound selected from the group consisting of 1, 1-Ac, A1, A2, A3, A4, A5, A6, A7, and A8: 
       
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         2 . The compound of  claim 1 , wherein R 20 , R 23 , and R 24  are each hydrogen; R 19  and R 21  are each independently R 29 ; and R 22  is —CH 2 R 29 , —CH 2 OR 29 ; or R 19  and R 21  taken together with the carbon atoms to which they are attached to form a 5-6 membered heterocyclyl optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from R 25 . 
     
     
         3 . The compound of  claim 1 , wherein the compound has Formula II: 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt thereof, wherein: 
         R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9  are each independently hydrogen, alkyl, akenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, aralkyl, heteroaryl, haloalkyl, halogen, cyano, NO 2 , —OR 26 , —C(═O)R 27 , —C(═O)N(R 26 )R 27 , —C(═O)OR 26 , —OC(═O)R 26 , —OSi(R 25 )(R 26 )R 27 , —S(═O) 2 R 26 , —S(═O) 2 N(R 26 )R 27 , —N(R 26 )R 27 , —N(R 26 )N(R 26 )R 27 , —N(R 26 )C(═O)R 27 , —N(R 26 )S(═O) 2 R 27  or a moiety comprising 1 to 30 plural valence atoms selected from the group consisting of carbon, nitrogen, oxygen and sulfur; or R 1  and R 2 , R 2  and R 3 , R 3  and R 4 , R 5  and R 6 , R 6  and R 7 , R 7  and R 8 , or R 8  and R 9  taken together with the carbon atoms to which they are attached to form a cyclic group which is optionally substituted with halogen or a moiety comprising 1 to 30 plural valence atoms selected from the group consisting of carbon, nitrogen, oxygen and sulfur; 
         R 10  and R 11  taken together form oxo; or while one of R 10  and R 11  is hydrogen, the other one of R 10  and R 11  is selected from the group consisting of R 25 , —OR 25 , —C(═O)R 25 , and —C(═O)OR 25 ; 
         R 19  is selected from the group consisting of R 25 , —OR 25 , —OC(═O)R 25 , —OC(═O)N(R 25 )R 25 , optionally substituted monosaccharide, optionally substituted disaccharide, optionally substituted trisaccharide, and optionally substituted tetrasaccharide; 
         R 21  is selected from the group consisting of R 25 , —OR 25 , —OC(═O)R 25 , —OC(═O)N(R 25 )R 25 , —C(═O)OR 25 , —CH 2 R 29 , —CH 2 OR 29 , —C(═O)R 29 ; or R 19  and R 21  taken together with the carbon atoms to which they are attached to form a 5-6 membered heterocyclyl optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from R 25 ; 
         R 25  for each occurrence is independently selected from hydrogen, halogen, trichloromethyl, trifluoromethyl, cyano, nitro, —OR 26 , —C(═O)R 27 , —C(═O)N(R 26 )R 27 , —C(═O)OR 26 , —OC(═O)R 26 , —OSi(R 25 )(R 26 )R 27 , —S(═O) 2 R 26 , —S(═O) 2 N(R 26 )R 27 , —N(R 26 )R 27 , —N(R 26 )N(R 26 )R 27 , —N(R 26 )C(═O)R 27 , —N(R 26 )S(═O) 2 R 27 , —N 3 , —OS(═O) 2 CF 3 , hydrocarbyl optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from the group consisting of R 28 , heterocyclcyl optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from the group consisting of R 28 , and —(CH 2 ) k -heterocyclyl optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from the group consisting of R 28 , wherein k is an integer between 1 and 6; 
         R 26  and R 27  for each occurrence are each independently hydrogen or selected from hydrocarbyl and heterocyclyl, either of which is optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from halogen, cyano, amino, hydroxy, C 1-6  alkyl and C 1-6  alkoxy; 
         R 28  for each occurrence is independently selected from halogen, trichloromethyl, trifluoromethyl, cyano, nitro, oxo, ═NR 26 , —OR 26 , —C(═O)R 27 , —C(═O)N(R 26 )R 27 , —C(═O)OR 26 , —OC(═O)R 26 , —OSi(R 25 )(R 26 )R 27 , —S(═O) 2 R 26 , —S(═O) 2 N(R 26 )R 27 , —N(R 26 )R 27 , —N(R 26 )N(R 26 )R 27 , —N(R 26 )C(═O)R 27  and —N(R 26 )S(═O) 2 R 27 ; and 
         R 29  for each occurrence is independently selected from hydrogen, halogen, trichloromethyl, trifluoromethyl, cyano, nitro, —OR 26 , —C(═O)R 27 , —C(═O)N(R 26 )R 27 , —C(═O)OR 26 , —OC(═O)R 26 , —OSi(R 25 )(R 26 )R 27 , —S(═O) 2 R 26 , —S(═O) 2 N(R 26 )R 27 , —N(R 26 )R 27 , —N(R 26 )N(R 26 )R 27 , —N(R 26 )C(═O)R 27 , —N(R 26 )S(═O) 2 R 27 , —N 3 , —OS(═O) 2 CF 3 , optionally substituted monosaccharide, optionally substituted disaccharide, optionally substituted trisaccharide, optionally substituted tetrasaccharide, hydrocarbyl optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from the group consisting of R 28 , and heterocyclyl optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from the group consisting of R 28 . 
       
     
     
         4 . The compound of  claim 3 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9  are each independently hydrogen, alkyl, akenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, aralkyl, heteroaryl, haloalkyl, halogen, cyano, NO 2 , —OR 26 , —C(═O)R 27 , —C(═O)N(R 26 )R 27 , —C(═O)OR 26 , —OC(═O)R 26 , —OSi(R 25 )(R 26 )R 27 , —S(═O) 2 R 26 , —S(═O) 2 N(R 26 )R 27 , —N(R 26 )R 27 , —N(R 26 )N(R 26 )R 27 , —N(R 26 )C(═O)R 27 , and —N(R 26 )S(═O) 2 R 27 ; or R 1  and R 2 , R 2  and R 3 , R 3  and R 4 , R 5  and R 6 , R 6  and R 7 , R 7  and R 8 , or R 8  and R 9  taken together with the carbon atoms to which they are attached to form a 5-membered heterocyclyl;
 R 10  and R 11  taken together form oxo; 
 R 19  is selected from the group consisting of OR 25 , —OC(═O)R 25 , —OC(═O)N(R 25 )R 25 , optionally substituted monosaccharide, optionally substituted disaccharide, optionally substituted trisaccharide, and optionally substituted tetrasaccharide; and 
 R 21  is selected from the group consisting of —OR 25 , —OC(═O)R 25 , —OC(═O)N(R 25 )R 25 ; or R 19  and R 21  taken together with the carbon atoms to which they are attached to form a 5 membered heterocyclyl optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from R 25 . 
 
     
     
         5 . The compound of  claim 1 , wherein the compound has Formula III: 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt thereof, wherein: 
         wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9  are each independently hydrogen, alkyl, akenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, aralkyl, heteroaryl, haloalkyl, halogen, cyano, NO 2 , —OR 26 , —C(═O)R 27 , —C(═O)N(R 26 )R 27 , —C(═O)OR 26 , —OC(═O)R 26 , —OSi(R 25 )(R 26 )R 27 , —S(═O) 2 R 26 , —S(═O) 2 N(R 26 )R 27 , —N(R 26 )R 27 , —N(R 26 )N(R 26 )R 27 , —N(R 26 )C(═O)R 27 , —N(R 26 )S(═O) 2 R 27 ; or R 8  and R 2 , R 2  and R 3 , R 3  and R 4 , R 5  and R 6 , R 6  and R 7 , R 7  and R 8 , or R 8  and R 9  taken together with the carbon atoms to which they are attached to form a 5-membered heterocyclyl; 
         R 25  for each occurrence is independently selected from hydrogen and hydrocarbyl optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from the group consisting of R 28 , heterocyclcyl optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from the group consisting of R 28 , and —(CH 2 ) k -heterocyclyl optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from the group consisting of R 28 , wherein k is an integer between 1 and 6; 
         R 26  and R 27  for each occurrence are each independently hydrogen or selected from hydrocarbyl and heterocyclyl, either of which is optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from halogen, cyano, amino, hydroxy, C 1-6  alkyl and C 1-6  alkoxy; 
         R 28  for each occurrence is independently selected from halogen, trichloromethyl, trifluoromethyl, cyano, nitro, oxo, ═NR 26 , —OR 26 , —C(═O)R 27 , —C(═O)N(R 26 )R 27 , —C(═O)OR 26 , —OC(═O)R 26 , —OSi(R 25 )(R 26 )R 27 , —S(═O) 2 R 26 , —S(═O) 2 N(R 26 )R 27 , —N(R 26 )R 27 , —N(R 26 )N(R 26 )R 27 , —N(R 26 )C(═O)R 27  and —N(R 26 )S(═O) 2 R 27 ; and 
         R 29  is selected from the group consisting of halogen, cyano, —OR 26 , —OC(═O)R 26 , —OSi(R 25 )(R 26 )R 27 , —N(R 26 )R 27 , —N(R 26 )N(R 26 )R 27 , —N(R 26 )C(═O)R 27 , —N(R 26 )S(═O) 2 R 27 , —N 3 , and —OS(═O) 2 CF 3 . 
       
     
     
         6 . The compound of  claim 5 , wherein R 1 , R 4 , R 6 , and R 9  are each hydrogen; R 2 , R 3 , R 7 , and R 8  are each independently —OR 26 ; and R 5  is hydrogen or —OR 26 ; or R 2  and R 3  taken together with the carbon atoms to which they are attached to form a 5-membered heterocyclyl; or R 7  and R 8  taken together with the carbon atoms to which they are attached to form a 5-membered heterocyclyl. 
     
     
         7 . The compound of  claim 1 , wherein the compound has Formula IV: 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt thereof, wherein: 
         R 2 , R 3 , R 7 , and R 8  are each independently —OR 26 ; and R 5  is hydrogen or —OR 26 ; or R 2  and R 3  taken together form a methylenedioxy group; or R 7  and R 8  taken together form a methylenedioxy group; 
         R 25  for each occurrence is independently selected from hydrogen and hydrocarbyl; 
         R 26  for each occurrence is independently hydrogen, hydrocarbyl, or heterocyclyl; and 
         R 29  is selected from the group consisting of halogen, cyano, —OR 26 , —OC(═O)R 26 , —OSi(R 25 )(R 26 )R 27 , —N(R 26 )R 27 , —N(R 26 )N(R 26 )R 27 , —N(R 26 )C(═O)R 27 , —N(R 26 )S(═O) 2 R 27 , —N 3 , and —OS(═O) 2 CF 3 . 
       
     
     
         8 . The compound of  claim 1 , wherein the compound has Formula V: 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt thereof, wherein: 
         wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9  are each independently hydrogen, alkyl, akenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, aralkyl, heteroaryl, haloalkyl, halogen, cyano, NO 2 , —OR 26 , —C(═O)R 27 , —C(═O)N(R 26 )R 27 , —C(═O)OR 26 , —OC(═O)R 26 , —OSi(R 25 )(R 26 )R 27 , —S(═O) 2 R 26 , —S(═O) 2 N(R 26 )R 27 , —N(R 26 )R 27 , —N(R 26 )N(R 26 )R 27 , —N(R 26 )C(═O)R 27 , —N(R 26 )S(═O) 2 R 27 ; or R 1  and R 2 , R 2  and R 3 , R 3  and R 4 , R 5  and R 6 , R 6  and R 7 , R 7  and R 8 , or R 1  and R 9  taken together with the carbon atoms to which they are attached to form a 5-membered heterocyclyl; 
         R 19  is selected from the group consisting of —OR 25 , —OC(═O)R 25 , —OC(═O)N(R 25 )R 25 , optionally substituted monosaccharide, optionally substituted disaccharide, optionally substituted trisaccharide, and optionally substituted tetrasaccharide; 
         R 21  is selected from the group consisting of —OR 25 , —OC(═O)R 25 , —OC(═O)N(R 25 )R 25 , and —C(═O)OR 25 ; 
         R 25  for each occurrence is independently selected from hydrogen and hydrocarbyl optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from the group consisting of R 28 , heterocyclcyl optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from the group consisting of R 28 , and —(CH 2 ) k -heterocyclyl optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from the group consisting of R 28 , wherein k is an integer between 1 and 6; 
         R 26  and R 27  for each occurrence are each independently hydrogen or selected from hydrocarbyl and heterocyclyl, either of which is optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from halogen, cyano, amino, hydroxy, C 1-6  alkyl and C 1-6  alkoxy; 
         R 28  for each occurrence is independently selected from halogen, trichloromethyl, trifluoromethyl, cyano, nitro, oxo, ═NR 26 , —OR 26 , —C(═O)R 27 , —C(═O)N(R 26 )R 27 , —C(═O)OR 26 , —OC(═O)R 26 , —OSi(R 25 )(R 26 )R 27 , —S(═O) 2 R 26 , —S(═O) 2 N(R 26 )R 27 , —N(R 26 )R 27 , —N(R 26 )N(R 26 )R 27 , —N(R 26 )C(═O)R 27  and —N(R 26 )S(═O) 2 R 27 ; and 
         R 29  is selected from the group consisting of halogen, cyano, —OR 26 , —OC(═O)R 26 , —OSi(R 25 )(R 26 )R 27 , —N(R 26 )R 27 , —N(R 26 )N(R 26 )R 27 , —N(R 26 )C(═O)R 27 , —N(R 26 )S(═O) 2 R 27 , —N 3 , and —OS(═O) 2 CF 3 , optionally substituted monosaccharide, optionally substituted disaccharide, optionally substituted trisaccharide, and optionally substituted tetrasaccharide. 
       
     
     
         9 . The compound of  claim 8 , wherein R 1 , R 4 , R 6 , and R 9  are each hydrogen; R 2 , R 3 , R 7 , and R 8  are each independently —OR 26 ; and R 5  is hydrogen or —OR 26 ; or R 2  and R 3  taken together with the carbon atoms to which they are attached to form a 5-membered heterocyclyl; or R 7  and R 8  taken together with the carbon atoms to which they are attached to form a 5-membered heterocyclyl. 
     
     
         10 . The compound of  claim 1 , wherein the compound has Formula VI: 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt thereof, wherein: 
         R 2 , R 3 , R 7 , and R 8  are each independently —OR 26 ; and R 5 ; or R 2  and R 3  taken together form a methylenedioxy group; or R 7  and R 8  taken together form a methylenedioxy group; 
         R 9  is hydrogen or —OR 26 ; 
         R 19  is selected from the group consisting of —OR 25 , —OC(═O)R 25 , and —OC(═O)N(R 25 )R 25 , optionally substituted monosaccharide, optionally substituted disaccharide, optionally substituted trisaccharide, and optionally substituted tetrasaccharide; 
         R 21  is selected from the group consisting of —OR 25 , —OC(═O)R 25 , —OC(═O)N(R 25 )R 25 , and —C(═O)OR 25 ; 
         R 25  for each occurrence is independently selected from hydrogen and hydrocarbyl; 
         R 26  for each occurrence is independently hydrogen, hydrocarbyl, or heterocyclyl; and 
         R 29  is selected from the group consisting of halogen, cyano, —OR 26 , —OC(═O)R 26 , —OSi(R 25 )(R 26 )R 27 , —N(R 26 )R 27 , —N(R 26 )N(R 26 )R 27 , —N(R 26 )C(═O)R 27 , —N(R 26 )S(═O) 2 R 27 , —N 3 , and —OS(═O) 2 CF 3 , optionally substituted monosaccharide, optionally substituted disaccharide, optionally substituted trisaccharide, and optionally substituted tetrasaccharide. 
       
     
     
         11 . The compound of  claim 1 , wherein the compound is selected from the group consisting of 8, 9, 10, 11, 12, 16, 17, 18, 19, 20, 21, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53 and 54: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt thereof. 
       
     
     
         12 . A pharmaceutical composition comprising a compound of  claim 1  and at least one pharmaceutically acceptable excipient. 
     
     
         13 . A compound of  claim 1  for use in the treatment, prevention or delay of progression of a viral infection in a subject in need thereof. 
     
     
         14 . The use of  claim 13 , wherein the viral infection is human immunodeficiency virus (HIV), influenza, vesicular stomatitis virus (VSV), or coronavirus (CoV). 
     
     
         15 . The use of  claim 14 , wherein the influenza is avian influenza virus (AIV). 
     
     
         16 . The use of  claim 15 , wherein the AIV is influenza A. 
     
     
         17 . The use of  claim 16 , wherein the influenza A is H 5 N 1 . 
     
     
         18 . The use of  claim 14 , wherein the CoV is severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2). 
     
     
         19 . The use of  claim 13 , wherein the compound inhibits the viral replication. 
     
     
         20 . The use of  claim 13 , wherein the subject is human. 
     
     
         21 . The use of  claim 13 , wherein the subject is an animal. 
     
     
         22 . A compound for use in treatment, prevention or delay of progression of a viral infection in a subject in need thereof, wherein the compound has the Formula (I): 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt thereof, wherein: 
         X is oxygen or sulfur; 
         R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9  are each independently hydrogen, alkyl, akenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, aralkyl, heteroaryl, haloalkyl, halogen, cyano, NO 2 , —OR 26 , —C(═O)R 27 , —C(═O)N(R 26 )R 27 , —C(═O)OR 26 , —OC(═O)R 26 , —OSi(R 25 )(R 26 )R 27 , —S(═O) 2 R 26 , —S(═O) 2 N(R 26 )R 27 , —N(R 26 )R 27 , —N(R 26 )N(R 26 )R 27 , —N(R 26 )C(═O)R 27 , —N(R 26 )S(═O) 2 R 27  or a moiety comprising 1 to 30 plural valence atoms selected from the group consisting of carbon, nitrogen, oxygen and sulfur; or R 1  and R 2 , R 2  and R 3 , R 3  and R 4 , R 5  and R 6 , R 6  and R 7 , R 7  and R 8 , or R 8  and R 9  taken together with the carbon atoms to which they are attached to form a cyclic group which is optionally substituted with halogen or a moiety comprising 1 to 30 plural valence atoms selected from the group consisting of carbon, nitrogen, oxygen and sulfur; 
         R 10  and R 11  taken together form oxo; or while one of R 10  and R 11  is hydrogen or halogen, the other one of R 10  and R 11  is selected from the group consisting of R 25 , —OR 25 , —C(═O)R 25 , and —C(═O)OR 25 ; 
         R 12  and R 13  taken together form oxo; or while one of R 12  and R 13  is hydrogen or halogen, the other one of R 12  and R 13  is selected from the group consisting of R 25 , —OR 25 , —C(═O)R 25 , and —C(═O)OR 25 ; 
         R 19  and R 20  taken together form oxo; or while one of R 19  and R 20  is hydrogen or halogen, the other one of R 19  and R 20  is selected from the group consisting of R 25 , —OR 25 , —C(═O)R 25 , —C(═O)OR 25 , —OC(═O)R 25 , —OC(═O)N(R 25 )R 25 , optionally substituted monosaccharide, optionally substituted disaccharide, optionally substituted trisaccharide, and optionally substituted tetrasaccharide; 
         R 21  and R 22  taken together form oxo; or while one of R 21  and R 22  is hydrogen, halogen, R 25  or —OR 25 , the other one of R 21  and R 22  is selected from the group consisting of R 25 , —OR 25 , —OC(═O)R 25 , —OC(═O)N(R 25 )R 25 , —C(═O)OR 25 , —CH 2 R 29 , —CH 2 OR 29 , —C(═O)R 29 ; or R 19  and R 21  taken together with the carbon atoms to which they are attached to form a 5-6 membered heterocyclyl optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from R 25 ; 
         R 23  and R 24  taken together form oxo; or while one of R 23  and R 24  is hydrogen or halogen, the other one of R 23  and R 24  is selected from the group consisting of R 25 , —OR 25 , —C(═O)R 25 , —C(═O)OR 25 , optionally substituted monosaccharide, optionally substituted disaccharide, optionally substituted trisaccharide, and optionally substituted tetrasaccharide; 
         R 25  for each occurrence is independently selected from hydrogen, halogen, trichloromethyl, trifluoromethyl, cyano, nitro, —OR 26 , —C(═O)R 27 , —C(═O)N(R 26 )R 27 , —C(═O)OR 26 , —OC(═O)R 26 , —OSi(R 25 )(R 26 )R 27 , —S(═O) 2 R 26 , —S(═O) 2 N(R 26 )R 27 , —N(R 26 )R 27 , —N(R 26 )N(R 26 )R 27 , —N(R 26 )C(═O)R 27 , —N(R 26 )S(═O) 2 R 27 , —N 3 , —OS(═O) 2 CF 3 , hydrocarbyl optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from the group consisting of R 28 , heterocyclcyl optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from the group consisting of R 28 , and —(CH 2 ) k -heterocyclyl optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from the group consisting of R 28 , wherein k is an integer between 1 and 6; 
         R 26  and R 27  for each occurrence are each independently hydrogen or selected from hydrocarbyl and heterocyclyl, either of which is optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from halogen, cyano, amino, hydroxy, C 1-6  alkyl and C 1-6  alkoxy; 
         R 28  for each occurrence is independently selected from halogen, trichloromethyl, trifluoromethyl, cyano, nitro, oxo, ═NR 26 , —OR 26 , —C(═O)R 27 , —C(═O)N(R 26 )R 27 , —C(═O)OR 26 , —OC(═O)R 26 , —OSi(R 25 )(R 26 )R 27 , —S(═O) 2 R 26 , —S(═O) 2 N(R 26 )R 27 , —N(R 26 )R 27 , —N(R 26 )N(R 26 )R 27 , —N(R 26 )C(═O)R 27  and —N(R 26 )S(═O) 2 R 27 ; and 
         R 29  for each occurrence is independently selected from hydrogen, halogen, trichloromethyl, trifluoromethyl, cyano, nitro, —OR 26 , —C(═O)R 27 , —C(═O)N(R 26 )R 27 , —C(═O)OR 26 , —OC(═O)R 26 , —OSi(R 25 )(R 26 )R 27 , —S(═O) 2 R 26 , —S(═O) 2 N(R 26 )R 27 , —N(R 26 )R 27 , —N(R 26 )N(R 26 )R 27 , —N(R 26 )C(═O)R 27 , —N(R 26 )S(═O) 2 R 27 , —N 3 , —OS(═O) 2 CF 3 , optionally substituted monosaccharide, optionally substituted disaccharide, optionally substituted trisaccharide, optionally substituted tetrasaccharide, hydrocarbyl optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from the group consisting of R 28 , and heterocyclyl optionally substituted with 1, 2, 3, 4 or 5 group(s) independently selected from the group consisting of R 28 . 
       
     
     
         23 . The use of  claim 22 , wherein the compound is selected from the group consisting of 1, 1-Ac, A1, A2, A3, A4, A5, A6, A7, A8, 8, 9, 10, 11, 12, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53 and 54: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         24 . The use of  claim 22 , wherein the viral infection is HIV, influenza, VSV, or CoV. 
     
     
         25 . The use of  claim 24 , wherein the influenza is AIV. 
     
     
         26 . The use of  claim 25 , wherein the AIV is influenza A. 
     
     
         27 . The use of  claim 26 , wherein the influenza A is H5N1. 
     
     
         28 . The use of  claim 24 , wherein the CoV is SARS-CoV-2. 
     
     
         29 . The use of  claim 23 , wherein the compound inhibits the viral replication. 
     
     
         30 . The use of  claim 23 , wherein the subject is human. 
     
     
         31 . The use of  claim 23 , wherein the subject is an animal. 
     
     
         32 . The use of  claim 24 , wherein the compound is present in a separated extract or fraction from a plant material.